The orthoester Johnson–Claisen rearrangement of allylic terpenols in the presence of acidic ionic liquid

The orthoester Johnson–Claisen rearrangement of allylic terpenols in the presence of acidic ionic liquid Full article

Journal

Journal of Fluorine Chemistry
ISSN: 1873-3328 , E-ISSN: 0022-1139

Output data

Year: 2016, Volume: 183, Pages: 23-29 Pages count : 7 DOI: 10.1016/j.jfluchem.2016.01.005

Authors

Kryshtal Galina V. ¹ , Zhdankina Galina M. ¹ , Ignat’ev Nikolai V. ² , Schulte Michael ² , Zlotin Sergei G. ¹

Affiliations

1	N.D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow 119991, Russia
2	Merck KGaA, Frankfurter Strasse 250, D-64293 Darmstadt, Germany

A convenient protocol for the synthesis of natural isoprenoid-derived carboxylic esters via reaction of allylic terpenols with triethyl orthoacetate (propionate) in the presence of 1-butyl-3-methylimidazolium hexafluorophosphate, [bmim][PF6] (10 mol%), has been developed. The desired terpene derivatives were prepared in moderate to high yield. The ionic liquid (IL) can be easily separated from the products and repeatedly used up to ten times without reduction in the product yield. Experimental data evidence that HF, generated in situ from the IL, most likely acts as a true catalyst in the Johnson–Claisen rearrangement.

Kryshtal G.V. , Zhdankina G.M. , Ignat’ev N.V. , Schulte M. , Zlotin S.G.
The orthoester Johnson–Claisen rearrangement of allylic terpenols in the presence of acidic ionic liquid
Journal of Fluorine Chemistry. 2016. V.183. P.23-29. DOI: 10.1016/j.jfluchem.2016.01.005 WOS Scopus OpenAlex

Web of science:	WOS:000374607900004
Scopus:	2-s2.0-84956473122
OpenAlex:	W2239518718

DB	Citing
OpenAlex	9
Scopus	6
Web of science	6